The Calgary Herald, Mining and Ranche Advocate and General Advertiser started publication on 31 August 1883 in a tent at the junction of the Bow and Elbow by Thomas Braden, a school teacher, and his friend, Andrew Armour, a printer, and financed by "a five-hundred- dollar interest-free loan from a Toronto milliner, Miss Frances Ann Chandler.

In July 2000, CanWest Global made Canadian media history with its $3.5 billion purchase of Hollinger's newspaper and internet assets, acquiring "136 daily and weekly newspapers," [which included the Calgary Herald and] half of The National Post, 13 large big-city dailies, 85 trade publications and directories in the Southam Magazine and Information Group.

"[3][7][8] By 2003, Izzy Asper had built "CanWest Global into a profitable media powerhouse with annual revenues in excess of $2 billion and net earnings of $90 million.

[3][10][11] Postmedia, backed by a New York hedge fund, holds some of Canada's largest daily newspapers, including the Post, Vancouver Sun, Calgary Herald, and Ottawa Citizen.

[11] CEP union spokesman Peter Murdoch said, "This is hardly of net benefit to Canadians, their communities or the critical flow of information in a democratic society.

"[10] Since it emerged from bankruptcy court protection in July, 2010, Postmedia has erased 750 jobs, or 14 per cent of its work force, bringing to 1,700 the total number of staff eliminated at the company since 2008.By 2011, the Calgary Herald newsroom was remodelled to enable teams to work on its websites and social media platforms like Twitter as advertising revenue migrated from printed to digital media.

Swanson oversaw the move of their headquarters from downtown Calgary to a "$70 million plant on a hill overlooking the intersection of Deerfoot and Memorial.

"[U]nder his leadership, the Herald revamped every area of content, re-engineered its circulation function, and completely reorganized the complex process of selling, designing, and placing customers' advertising.

[15]: 17  In his report entitled "Exposing the Boss: A Study in Canadian Journalism Ethics" journalist Bob Bergen argued that there were dramatic changes during this period.

In the spring of 2005, the Herald joined several other CanWest Global affiliates in launching Dose, a free daily newspaper targeted at younger commuters; it was discontinued as a print publication after a year.

In August 2010 Paul Godfrey President and CEO of Postmedia Network announced the appointment of Guy Huntingford as the publisher of the Calgary Herald as it "continues its transformation into an integrated multimedia brand.

"[18] In April 2013 Godfrey announced that was "eliminating the publisher position at its chain of 10 newspapers, which includes the National Post, the Montreal Gazette, the Ottawa Citizen" and the Calgary Herald in a cost-cutting measure.

[10] A June 2010 series, "Worked to Death" on the "human costs of Alberta's economic boom" by Chris Varcoe and research by Kelly Cryderman and Renata D'Aliesio, won the 2010 Michener Award, one of the highest distinctions in Canadian journalism.

In his June 14, 2011 acceptance speech, Varcoe acknowledged the support of the newspaper, particularly editors Lorne Motley and Monica Zurowski, who invested resources for over a year to "important civic journalism".